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Like Eli35, I would suggest starting with small expenditures and working your way up if you aren't satisfied, this rabbit hole is extremely deep. Plug your IEM's into your sources, do you hear any hiss/static/hum? Make sure to move about the system without having music playing (open programs/apps, navigate through web browsers, etc... You will typically expose any "noise" within your source in this manner. If you have no issues then I would suggest just an amp (O2, Magni, FiiO). If you have a noisy source then look at getting an outboard DAC/Amp or DAC + AMP stack (preferably driven by wall power, not USB). I started small and now have 20+ pairs of headphones, three amps, one usb amp/dac, an outboard rack sized DAC and another on the way. It took me over a decade to build my collection, as I identified "flaws" in my chain I updated it.
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